This invention relates to insecticidal, miticidal, fungicidal and ovicidal sulfonamides, agricultural compositions containing them and methods of using them.
Belgian Pat. No. 826,376, discloses diphenylamine derivatives of the formula: ##STR1## wherein R is hydrogen, C.sub.1-6 alkyl or alkoxy;
X is halogen; PA1 m is zero or an integer from one to three; PA1 n is zero or one; PA1 p is zero, one or two; PA1 q is zero, one or two; and PA1 the sum of m, n, p and q is one, two or three. PA1 R.sup.2 is H, halogen, CN, NO.sub.2 and/or alkyl optionally substituted with halogen and/or haloalkoxy; or XR' and R.sup.2, when ortho to one another, may be linked so as to form (with the 2-adjacent C-atoms of the phenyl ring) an optionally substituted dioxanyl ring. PA1 R.sub.2 is H, F, Cl, Br, NO.sub.2, CF.sub.3 or S(O).sub.k R.sub.9 ; PA1 R.sub.5 is H, Cl, F, Br or NO.sub.2 ; PA1 Z is --NR.sub.6 SO.sub.2 R.sub.13, ##STR4## R.sub.6 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.4 chloroalkyl, ##STR5## or R.sub.14 CHCOR.sub.15 ; R.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br or F; PA1 R.sub.8 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br, F, CF.sub.3, NO.sub.2, R.sub.11 S(O).sub.k or CO.sub.2 R.sub.12 ; PA1 R.sub.9 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 alkyl substituted with 2 to 4 atoms or Cl and/or F; PA1 R.sub.10 is H, NO.sub.2 or CF.sub.3 ; PA1 R.sub.11 is C.sub.1 -C.sub.2 alkyl or C.sub.2 -C.sub.4 dialkylamino, PA1 R.sub.12 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.13 is ##STR6## naphthyl, NR.sub.16 R.sub.17, CF.sub.3 or C.sub.1 -C.sub.20 alkyl; R.sub.14 is H or CH.sub.3 ; PA1 R.sub.15 is C.sub.1 -C.sub.4 alkoxy or N(R.sub.17).sub.2 ; PA1 R.sub.16 is C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or ##STR7## R.sub.17 is C.sub.1 -C.sub.3 alkyl; R.sub.18 is H, C.sub.1 -C.sub.8 alkyl, ##STR8## or NR.sub.16 R.sub.17 ; A is --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --X(CH.sub.2).sub.2 --, or --X(CH.sub.2).sub.3 --, where X is O, S or NR.sub.19 and where X is bonded to the carbonyl carbon of Z; PA1 R.sub.19 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted with 1 or 2 groups selected from F, Cl, Br, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.20 is NO.sub.2 or CF.sub.3 ; PA1 (1) at least two of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen; PA1 (2) no more than two of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are simultaneously NO.sub.2 or CF.sub.3 ; PA1 (3) when two NO.sub.2 or two S(O).sub.k R.sub.9 groups are present, they are not ortho to one another; PA1 (4) only one of R.sub.6 and R.sub.13 or one of R.sub.6 and R.sub.16 or one of R.sub.6 and R.sub.18 is ##STR9## (5) when R.sub.11 is dialkylamino, then k is 2; and (6) R.sub.10 and R.sub.20 are not simultaneously CF.sub.3 ; and further provided that when R.sub.10 is NO.sub.2, then PA1 (a) R.sub.1 is H, F or Cl when R.sub.3 is other than H, F or Cl; PA1 (b) when R.sub.1 =R.sub.3 =R.sub.5, then R.sub.1, R.sub.3 and R.sub.5 are either H or F; and PA1 (c) R.sub.5 is either H or F. PA1 R.sub.1 is F, Cl, Br, CF.sub.3, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k CF.sub.3 ; PA1 R.sub.2 is H, F, Cl or Br; PA1 R.sub.3 is H, F, Cl, Br or S(O).sub.k CF.sub.3 ; PA1 R.sub.4 is F, Cl, Br, CF.sub.3, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k CF.sub.3 ; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.7 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or Cl; PA1 R.sub.8 is H, C.sub.1 -C.sub.3 alkyl or Cl; PA1 R.sub.10 is NO.sub.2 ; and PA1 R.sub.13 is ##STR10## naphthyl, NR.sub.16 R.sub.17 or C.sub.1 -C.sub.3 alkyl, where R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.2 alkyl. PA1 R.sub.1 and R.sub.4 are independently Cl, CF.sub.3, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k CF.sub.3 ; PA1 R.sub.3 is H or S(O).sub.k CF.sub.3 ; PA1 R.sub.2 and R.sub.5 are H; and PA1 R.sub.13 is ##STR11## 2-naphthyl, N(CH.sub.3).sub.2 or CH.sub.3. PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-N-4-dimethylbenzenesulfonamide; PA1 N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluo romethyl)phenyl]aminothio]-2-methylbenzenesulfonamide; PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-4-methyl-N-(1-methylethyl)benzenesulfonamide; PA1 N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluo romethyl)phenyl]aminothio]-4-methylbenzenesulfonamide; PA1 N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluo romethyl)phenyl]aminothio]-benzenesulfonamide; PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-N-(4-methylphenylsulfonyl)glycine methyl ester; PA1 N-[N-[2,4-dinitro-6-trifluoromethyl)phenyl]-N-(2,4,6-trifluorophenyl)aminot hio]-N,4-dimethylbenzenesulfonamide; PA1 N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)ph enyl]-2-oxo-1-pyrrolidinesulfenamide; PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-N-methyl-2-naphthalenesulfonamide; PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-N-butyl-N',N'-dimethylsulfamide; PA1 N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluo romethyl)phenyl]aminothio]-methanesulfonamide. PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl )phenyl]aminothio]-N-(1,1-dimethylethyl)-4-methylbenzenesulfonamide; and PA1 N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-trifluoromethylp henyl]aminothio]-N-(2-methoxyethyl)-4-methylbenzenesulfonamide.
Specifically disclosed in U.K. Pat. No. 1,455,207 is the compound 2,5'-bistrifluoromethyl-2'-chloro-4,6-dinitrodiphenylamine. The compounds are taught to have insecticidal, acaricidal and fungicidal properties.
European Patent Office Application 156 discloses 2-anilino-3,5-dinitrobenzotrifluoride derivatives of the formula: ##STR2## wherein R' is alkyl substituted with halogen and/or haloalkoxy; phenyl optionally substituted with halogen, haloalkyl, haloalkoxy, haloalkylmercapto or haloalkylsulphonyl; or, when X=O, R' is unsubstituted alkyl;
The application teaches that the disclosed compounds have insecticidal, acaricidal, nematocidal, insect growth retardant, fungicidal and bactericidal activity.
A substantial portion of the world's food supply is destroyed by pests and plant diseases. There is thus a continuing need for highly active insecticides, miticides, ovicides and fungicides.